I installed and tested this plugin today. The set-up is a bit time consuming if you’re using the free version since you have to add dummy data by hand for 64 team names, but once you have that, the plugin will let you randomly fill in all the data for your dummy brackets (by hitting the randomize button). I love the fact that this plugin is free, too. It’s the ultimate freemium model. Do a lot of work by hand for free, or upgrade to let the plugin’s service do the work for you. If you do want to go with the free version, I wrote a quick guide on how to get it up and running: http://www.fredmarion.com/how-to-use-bracketpress-for-wordpress-for-free/
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